DETAILED ACTION
Notice of Pre-AIA or AIA Status
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Priority
This application claims benefit of provisional application 63/321,432 filed 03/18/2022. Applicant’s claim for the benefit of a prior-filed application under 35 U.S.C. 119(e) or under 35 U.S.C. 120, 121, 365(c), or 386(c) is acknowledged.
Status of the Claims
Claims 1 and 3-6 were amended. Claims 2 and 11-14 were cancelled. Claims 21-24 are new.
Claims 1, 3-10 and 15-24 are pending (claim set filed 08/05/2025) and are examined on the merits herein.
Withdrawal of Rejections
The response and amendment filed on 08/05/2025 are acknowledged. The Declaration of Professor Allgeier under 37 C.F.R. 1.132 is acknowledged. All of the amendment and arguments have been thoroughly reviewed and considered.
For the purposes of clarity of the record, the reasons for the Examiner's withdrawal and/or maintaining if applicable, of the substantive or essential claim rejections are detailed directly below and/or in the Examiner's response to arguments section.
Maintained/Modified Rejections
The following rejections are maintained and/or modified taking into consideration amendments to claims filed on 08/05/2025.
Claim Rejections - 35 USC § 103
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
Claims 1, 3-6, 10, 15-23 are rejected under 35 U.S.C. 103 as being unpatentable over Li (Li et al. Biodegradation, 2011, 22, 1227-1237 on record in IDS) in view of Leskovac (Leskovac et al. FEMS Yeast Research, 2002, 481-494 on record in IDS) and Clarizia (Clarizia et al. 2020, 393, 123425, 1-7) as evidenced by LibreTexts (LibreTexts, 2021 [retrieved on 10/17/2025]. Retrieved from the Internet: <https://bio.libretexts.org/Bookshelves/Cell_and_Molecular_Biology/Book%3A_Biofundamentals_(Klymkowsky_and_Cooper)/05%3A_Molecular_interactions_thermodynamics_and_reaction_coupling/5.05%3A_Coupling__reactions>).
Regarding claims 1, 20 and 21, Li teaches ethanol-dependent reduction of furfural by alcohol dehydrogenases (Title). Li discloses that yeast alcohol dehydrogenases, specifically YADH1, YADH6, and YADH7 (which are isozymes), are shown to reduce furfural with biocatalyst cofactors NADH for YADH1 and NADPH for YADH6, and YADH7 as the reducing power (p. 1228, left column, 2nd paragraph). Li describes that the coupled reaction for ethanol oxidation to acetaldehyde and furfural reduction to furfuryl alcohol, shown in Equations 4-6 (p. 1234, right column), provides a thermodynamically more favorable method of producing acetaldehyde from ethanol. Li discloses kinetic parameters for reaction of acetaldehyde production from ethanol with four alcohol dehydrogenases, one of which is YADH1 (p. 1233, Table 1). Further, Li teaches that YADH1 is constitutively expressed and its kinetic parameters for NADH-dependent reduction of furfural suggest that it can effectively catalyze furfural reduction at high furfural concentrations (p. 1236, left column, 2nd paragraph). Li describes reaction to comprise biocatalysts not immobilized but dispersed in the reaction mixture (p. 1229, right column, 2nd paragraph) that reads on claim 21. Therefore, Li teaches a method of producing acetaldehyde by exposing ethanol and furfural to a biocatalyst (YADH1) and a biocatalyst cofactor (NADH) dispersed in the reaction mixture to produce a product mixture comprising furfuryl alcohol and acetaldehyde.
Li does not teach yeast YADH2 and YADH3 as biocatalyst producing acetaldehyde. Although Li teaches concentration of acetaldehyde from the after reaction termination by HPLC (p. 1229, right column, 2nd paragraph), Li does not teach recovering of the acetaldehyde from the reaction mixture as it is being produced.
Leskovac teaches structure, function and mechanism of action of the three yeast alcohol dehydrogenase isoenzymes, YADH-1, YADH-2 and YADH-3 (Abstract). Leskovac describes that yeast alcohol dehydrogenases catalyze the reversible reaction of conversion of ethanol to acetaldehyde with NAD+ as a cofactor and determines kinetic parameters for that reaction for three isoenzymes (p. 482, left column 1st paragraph and Table 1). Leskovac discloses that YADH-1 and YADH-3 have very similar kinetic characteristics, while YADH-2 has a much higher substrate specificity for ethanol and acetaldehyde, and much lower Michaelis constants with ethanol and acetaldehyde. It was found that for all alcohols, normalized rates with YADH-2 were about three-fold faster than with YADH-1 (p. 482, left column, 1st paragraph).
Clarizia teaches efficient recovery and purification of acetaldehyde during ethanol oxidation by removing acetaldehyde from the solution carried out by injecting an inert gas (nitrogen) bubbling into the solution and collecting the gas by feeding the resulting gaseous stream to an absorber, in which acetaldehyde is captured by the aqueous stream (Abstract, p. 6, right column, 6th paragraph). Clarizia discloses that almost all acetaldehyde produced by ethanol oxidation (93%) was separated from the aqueous mixture after using inert gas stripping (p. 5, left column, 3rd paragraph).
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to modify the coupled reaction method of Li to include isozymes YADH2 and YADH3 taught by Leskovac and try to use three isoenzymes together. One would have been motivated to do so since all three isoenzymes were shown by Leskovac to produce acetaldehyde, Leskovac teaches that YADH3 has similar kinetic characteristics as YADH1 and since it is expected to perform similarly in the coupled reaction method of Li and YADH2 has a much higher substrate specificity for ethanol and acetaldehyde, and much lower Michaelis constants with ethanol and acetaldehyde and can increase efficiency of acetaldehyde production in coupled method of Li. A skilled artisan would have reasonably expected success in the combination because Li and Leskovac teach yeast alcohol dehydrogenases producing acetaldehyde.
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to combine the teachings of Li, Leskovac and Clarizia and add the recovery of acetaldehyde described by Clarizia to the coupled reaction method based on Li and Leskovac teachings. One would have been motivated to do so since Clarizia teaches that almost all (93%) acetaldehyde produced was separated from the aqueous mixture after using inert gas stripping. A skilled artisan would have reasonably expected success in the combination because Li, Leskovac and Clarizia teach production of acetaldehyde from ethanol. Thus, teachings of Li, Leskovac and Clarizia render claims 1, 20 and 21 obvious.
Regarding claim 10, Li teaches that lignocellulosic biomasses can be converted into sugars and sugar derivatives, such as furfural, wherein the sugars may be fermented into ethanol (Abstract). Thus, teachings of Li, Leskovac and Clarizia render claim 10 obvious.
Regarding claims 3 and 6, Clarizia teaches the use of an inert gas containing nitrogen (p. 4, left column, last paragraph). Regarding claim 4-6, Clarizia teaches that the nitrogen stream is employed at 0.8 L/min and at a pressure of 1 atm (p, 4, right column, 1st paragraph) that reads on claimed limitations. Regarding claim 23, Clarizia teaches that almost all acetaldehyde produced by ethanol oxidation (93%) was separated from the aqueous mixture after using inert gas stripping (p. 5, left column, 3rd paragraph).
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to follow guidance of Clarizia and add step of recovery of acetaldehyde by injecting inert gas, nitrogen, at the specified parameters of flow rate and pressure to the coupled reaction method of acetaldehyde production based on Li and Leskovac teachings. One would have been motivated to do so since Clarizia teaches that almost all (93%) acetaldehyde produced was separated from the aqueous mixture after using inert gas stripping. A skilled artisan would have reasonably expected success in the combination because Li, Leskovac and Clarizia teach production of acetaldehyde from ethanol. Thus, teachings of Li, Leskovac and Clarizia render claims 3-6 and 23 obvious.
Regarding claims 15-19, the combination of prior art of Li, Leskovac and Clarizia teaches the claimed method for production of acetaldehyde from ethanol and renders claim 1 obvious as described above. Li teaches a method of producing acetaldehyde by exposing ethanol and furfural to a biocatalyst (YADH1) and a biocatalyst cofactor (NADH) to produce a product mixture comprising furfuryl alcohol and acetaldehyde. Leskovac describes three isozymes of YADH, YADH1, YADH2 and YADH3, from which YADH3 has the same kinetic parameters as YADH1 from Li teaching and YADH2 has a much higher substrate specificity for ethanol and acetaldehyde, much lower Michaelis constants with ethanol and acetaldehyde and is about three-fold faster than YADH1, providing motivation to include all three isoenzymes of YADH in the method for producing acetaldehyde of Li to increase its efficiency. Clarizia teaches efficient method of acetaldehyde recovery as it being produced with almost all (93%) acetaldehyde produced separated from the aqueous mixture after using inert gas stripping providing motivation to include the described recovery step to Li method of acetaldehyde production. Thus, combination of Li, Leskovac and Clarizia teach all the claimed limitations of the method of acetaldehyde production from ethanol of claim 1. Therefore, one of ordinary skill in the art would expect that the method of acetaldehyde production taught by Li, Leskovac and Clarizia would necessarily yield the claimed conversion for ethanol and furfural and selectivity for acetaldehyde and furfuryl alcohol. Thus, teachings of Li, Leskovac and Clarizia render claims 15-19 obvious.
Regarding claim 22, Li teaches coupled reactions for ethanol oxidation to acetaldehyde with reduction of NAD+ to NADH and furfural reduction to furfuryl alcohol with NADH oxidation to NAD+, shown in Equations 4-6 (p. 1234, right column, p. 1235, left column and Fig. 3). These reaction are reversible and work based on Le Chatelier’s principle as evidenced by LibreTexts (paragraphs 3 and 4), indicating that when the product of one reaction, e.g. acetaldehyde, is removed, production of both products of coupled reactions will increase to reach equilibrium, in instant case production of acetaldehyde and NADH will increase. It can be envisaged that the increase in NADH will result in the increase in the reaction of furfural reduction and higher yield of furfuryl alcohol will be produced.
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention that recovering of acetaldehyde from the reaction mixture during its production in coupled reaction of ethanol oxidation and furfural reduction based on Li, Leskovac and Clarizia teachings will increase the yield of furfural alcohol produced. One would have been motivated to assume so with reasonably expected success since acetaldehyde removal will shift the equilibrium of ethanol oxidation towards acetaldehyde and NADH production based on Le Chatelier’s principle as evidenced by LibreTexts and increase in NADH will shift equilibrium of furfural reduction towards higher yield of produced furfuryl alcohol. Thus, teachings of Li, Leskovac and Clarizia as evidenced by LibreTexts render claim 22 obvious.
Claims 7-9 and 24 are rejected under 35 U.S.C. 103 as being unpatentable over Li (Li et al. Biodegradation, 2011, 22, 1227-1237 on record in IDS) in view of Leskovac (Leskovac et al. FEMS Yeast Research, 2002, 481-494 on record in IDS) and Clarizia (Clarizia et al. 2020, 393, 123425, 1-7) as applied to claim 1 above, and further in view of Marques (Marques et al. Applied Surface Science, 2013, 275, 347-360) as evidenced by Shinde (Shinde et al. Biotechn. Reports, 2018, e00260, 1-7) and Sachdeva (Sachdeva et al. Green Process Synth., 2012, 1, 469-477).
The teachings of Li, Leskovac and Clarizia have been set forth above.
Li, Leskovac and Clarizia do not teach immobilization of the biocatalyst on a solid support.
Regarding claim 7-9, Marques teaches enzyme immobilization and chemical functionalization of surfaces (Abstract). Marques discloses the use of amine-functionalized solid supports of modified polystyrene and glutaraldehyde (GA) as a bi-functional cross linking agent for enzyme immobilization. The enzyme layer is covalently bonded to the amine group of the solid polystyrene support using the linker, glutaraldehyde (p. 350-351, section 2.4 and 2. 5). Marques describes that GA acts as a bifunctional linker, forming stable covalent bonds between the chemical groups from the support with amine group of the enzyme (p. 353, right column, 2nd paragraph) and mentions that the immobilized enzymes have retained their enzymatic activities (p. 355, left column, 3rd paragraph). Therefore, Marques teaches the claimed solid support for enzyme immobilization. Yeast alcohol dehydrogenase can be immobilized by its amine group with the linker GA as evidenced by Shinde (Abstract). Shinde mentions that immobilization increases YADH thermostability and reusability (Abstract).
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to use the immobilization method of Marques in the coupled reaction method of acetaldehyde production based on Li, Leskovac and Clarizia teachings. One would have been motivated to do so since Marques showed that GA acts as a bi-functional linker, forming stable covalent bonds between the chemical groups from the support with amine group of the enzyme and enzyme retains activity. YADH can be immobilized by its amine group via GA linker resulting in the increase in its thermostability and reusability as evidenced by Shinde. A skilled artisan would have reasonably expected success in the combination because Li, Leskovac and Clarizia provide method of acetaldehyde production from ethanol, Li and Leskovac teach YADH catalyzing that reaction, Shinde describes immobilization of YADH via GA linker and Marques provides method of enzyme immobilization on solid surface via GA linking. Thus, teachings of Li, Leskovac, Clarizia and Marques as evidenced by Shinde render claims 7-9 obvious.
Regarding claim 24, Marques teaches amine-functionalized solid supports for enzyme immobilization which are activated with glutaraldehyde. Marques describes that glutaraldehyde is removed by washing prior to binding the enzyme (p. 350, section 2.4). It can be envisaged that the solid support may have exposed amino groups not involved in the interaction with glutaraldehyde since the unreacted amino groups were not blocked prior to enzyme binding. As described for claim 7 above, the immobilization method of Marques can be used in the coupled reaction method of acetaldehyde production based on Li, Leskovac and Clarizia teachings. This method involves furfural as a substrate which has carbonyl group that can interact with amino group with formation of Schiff base as evidenced by Sachdeva. Sachdeva teaches that furfural and its derivatives efficiently bind to the amino group of alanine when stirring in aqueous solution at room temperature (p. 471, right column, 2nd paragraph, p. 474, left column, 1st paragraph, Table 1, 3g - furfural). Therefore, furfural present in the reaction mixture can bind to the unreacted amino groups of the surface with immobilized YADH isozymes.
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention that furfural present in the reaction mixture during acetaldehyde production based on Li, Leskovac and Clarizia teachings can bind to unreacted amino groups of the solid support used for enzyme immobilization as taught by Marques. One would have been motivated to assume so with reasonably expected success since furfural can interact with amino groups in aqueous solution at room temperature as evidenced by Sachdeva. Thus, teachings of Li, Leskovac, Clarizia and Marques as evidenced by Shinde and Sachdeva render claim 24 obvious.
Response to Arguments
Applicant's arguments filed 08/05/2025 have been fully considered but they are not persuasive.
In response to Applicant’s arguments (addressing p. 6-7 of the Remarks and paragraph 4 of the Declaration under 37 C.F.R. 1.132) that: “there is insufficient motivation to apply the teachings of Clarizia to Li/Leskovac and no reasonable expectation of success. … Clarizia's system is far less complex than the claimed method involving a set of three enzymes and a coupled chemical reaction cascade involving both the oxidation of ethanol to acetaldehyde and the reduction of furfural to furfuryl alcohol that leads to a product mixture containing the three enzymes, biocatalyst cofactor, unoxidized ethanol, unreduced furfural, furfuryl alcohol, and acetaldehyde. (Id.) Selective separation of acetaldehyde from such a product mixture is a substantially more complex and delicate process than that being considered in Clarizia. (Id.) Yet, nothing in Clarizia, Li, or Leskovac provides the person of ordinary skill with guidance for addressing this complexity. (Id.)”, these arguments are not persuasive because:
In response to applicant’s argument that there is no teaching, suggestion, or motivation to combine the references, the examiner recognizes that obviousness may be established by combining or modifying the teachings of the prior art to produce the claimed invention where there is some teaching, suggestion, or motivation to do so found either in the references themselves or in the knowledge generally available to one of ordinary skill in the art. See In re Fine, 837 F.2d 1071, 5 USPQ2d 1596 (Fed. Cir. 1988), In re Jones, 958 F.2d 347, 21 USPQ2d 1941 (Fed. Cir. 1992), and KSR International Co. v. Teleflex, Inc., 550 U.S. 398, 82 USPQ2d 1385 (2007). In this case, one would have been motivated to add the recovery of acetaldehyde described by Clarizia to the coupled reaction method based on Li and Leskovac teachings with reasonably expected success because Li, Leskovac and Clarizia teach production of acetaldehyde from ethanol and Clarizia discloses method allowing to separate almost all (93%) acetaldehyde produced from the aqueous mixture after using inert gas.
Applicant argues (addressing p. 7-10 of the Remarks and paragraphs 5-9 of the Declaration under 37 C.F.R. 1.132) that opposite to the expectation in the field that gas-water interface would lead to denaturation of the enzymes and immobilization is necessary to prevent denaturation, Inventors “were surprised that step (b) of the claimed method was successfully employed to achieve simultaneous recovery of acetaldehyde from the product mixture as it was being produced in step (a).” Applicants refer to Example 2 in the specification showing recovery of 56% of acetaldehyde from the reaction mixture, provide additional experimental data in the Declaration on “simultaneous recovery of acetaldehyde even without any biocatalyst immobilization.” and argue that: ”The data also shows an additional benefit that the conversion of furfural increases substantially as the acetaldehyde is simultaneously removed, further underscoring the unexpected nature of the claimed method.” Applicant further argues that the discussed unexpected results are claimed in new claims 21, 22 and 23. These arguments are not persuasive because:
The data in Example 2 show recovery of 56% of acetaldehyde after 180 min of flowing of nitrogen through the reaction mixture. The 56% recovery of acetaldehyde is claimed in claim 23. This result is not unexpected since Clarizia teaches 93% of produced acetaldehyde recovery after 120 min of stripping with nitrogen (p. 5, left column, 3rd paragraph). The data submitted in the Declaration do not provide the amount of recovered acetaldehyde, however, show increase in furfuryl alcohol generation with the simultaneous removal of acetaldehyde (which is also claimed in claim 22). Since the reaction of acetaldehyde production is coupled to furfural reduction (ethanol oxidation to acetaldehyde with reduction of NAD+ to NADH and furfural reduction to furfuryl alcohol with NADH oxidation to NAD+ as shown in Equations 4-6 of Li (p. 1234, right column, p. 1235, left column and Fig. 3)), it is not unexpected that removal of product of one reaction will increase production of the product of coupled reaction based on Le Chatelier’s principle as evidenced by LibreTexts (paragraphs 3 and 4). In instant case, one of ordinary skill in the art will realize that acetaldehyde removal will shift the equilibrium of ethanol oxidation towards acetaldehyde and NADH production and increase in NADH will shift equilibrium of furfural reduction towards higher yield of produced furfuryl alcohol.
The advantage of the recovering acetaldehyde from the reaction mixture as it is being produced recognized by the Applicant does not make the combination of prior art non-obvious because the prior art does not need to point out all advantages if there is a motivation to combine the prior art. MPEP 2145: “The fact that appellant has recognized another advantage which would flow naturally from following the suggestion of the prior art cannot be the basis for patentability when the differences would otherwise be obvious." Ex parte Obiaya, 227 USPQ 58, 60 (Bd. Pat. App. & Inter. 1985) (The prior art taught combustion fluid analyzers which used labyrinth heaters to maintain the samples at a uniform temperature. Although appellant showed that an unexpectedly shorter response time was obtained when a labyrinth heater was employed, the Board held this advantage would flow naturally from following the suggestion of the prior art.). See also Lantech Inc. v. Kaufman Co. of Ohio Inc., 878 F.2d 1446, 12 USPQ2d 1076, 1077 (Fed. Cir. 1989), cert. denied, 493 U.S. 1058 (1990) (unpublished — not citable as precedent) ("The recitation of an additional advantage associated with doing what the prior art suggests does not lend patentability to an otherwise unpatentable invention.")”. In instant case, Li, Leskovac and Clarizia teach production of acetaldehyde from ethanol and Clarizia discloses method allowing to separate almost all (93%) acetaldehyde produced from the aqueous mixture after using inert gas (p. 5, left column, 3rd paragraph) providing motivation to add acetaldehyde recovery to method of Li and Lescovac.
Assuming arguendo applicant has shown unexpected data, claims are not commensurate in scope with the unexpected results. MPEP 716.02: “Whether the unexpected results are the result of unexpectedly improved results or a property not taught by the prior art, the "objective evidence of nonobviousness must be commensurate in scope with the claims which the evidence is offered to support." In instant case, although the experimental data presented in the Declaration indicate enzyme mixture to retain activity during the simultaneous recovery of acetaldehyde with inert gas, the presented data are based on a very specific concentrations of ethanol, furfural, NAD+ and enzyme mixture and specific reaction parameters, e.g. time of reaction of 6 hours after the first addition of furfural and up-to 14 hours after the second addition of furfural. These concentrations and reaction parameters are not present in the claims 1, 21 and 22 and hence the claims are not commensurate in scope with the unexpected results.
Applicant argues (addressing p. 8 of the Remarks) that the use of large number of references (Li, Leskovac, Clarizia, Marques, and Shinde) “strongly suggests that impermissible hindsight in view of Applicants' own disclosure has been used in concluding obviousness. That is, even if isolated elements of the claimed method are found individually within these five different references, a prima facie case of obviousness requires a detailed explanation supported by evidence as to why the person of ordinary skill in the art would have thought to consider five disparate references and then would have gone through the additional effort and expense associated with combining the five references together.” In response to applicant's argument that the examiner has combined an excessive number of references, reliance on a large number of references in a rejection does not, without more, weigh against the obviousness of the claimed invention. See In re Gorman, 933 F.2d 982, 18 USPQ2d 1885 (Fed. Cir. 1991). In instant case, one would have been motivated to immobilize YADH used for acetaldehyde production based on combination of prior art of Li, Leskovac and Clarizia teachings because Shinde showed increase in YADH thermostability and reusability as a result of immobilization (Abstract) and Marques provided method of immobilization (Abstract) that retains enzyme activity (p. 355, left column, 3rd paragraph) and therefore immobilization of YADH is expected to increase efficiency of acetaldehyde production.
In response to Applicant’s arguments (addressing p. 10 of the Remarks) that: “new claim 24 … requires that the solid support comprises additional furfural covalently bound to surfaces of the solid support. Nothing in the cited prior art teaches or suggests this additional feature”, these arguments are not persuasive because: as described in the rejection above furfural present in the reaction mixture during acetaldehyde production as taught by Li (p. 1234, right column) can bind to unreacted amino groups of the solid support used for enzyme immobilization by Marques (p. 350, section 2.4) as evidenced by Sachdeva showing that furfural can interact with amino groups in aqueous solution at room temperature (p. 471, right column, 2nd paragraph, p. 474, left column, 1st paragraph, Table 1) .
Conclusion
No claims are allowed.
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to LIOUBOV G KOROTCHKINA whose telephone number is (571)270-0911. The examiner can normally be reached Monday-Friday: 8:00-5:30.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Sharmila G Landau can be reached at (571)272-0614. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/L.G.K./Examiner, Art Unit 1653 /SHARMILA G LANDAU/Supervisory Patent Examiner, Art Unit 1653
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